


Prison Break ... Not

by LazySintastic13 (EmeraldWriter)



Category: Undertale (Video Game)
Genre: Alternate Universe - Underfell, Anal Sex, Cock Warming, Creampie, Ecto-Penis (Undertale), Ecto-Tongue (Undertale), Ecto-Vagina (Undertale), Guard Sans ... ofc he is. Cough, Italian Mafia, M/M, Multiple Orgasms, Overstimulation, Prisoner Red, Rough Kissing, Rough Sex, Semi-Public Sex, Under-Desk Blow Jobs, Underfell Sans, Vaginal Sex, Wall Sex, dubcon
Language: English
Status: Completed
Published: 2018-06-22
Updated: 2018-06-22
Packaged: 2019-05-26 22:15:20
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,917
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15010592
Author URL: https://archiveofourown.org/users/EmeraldWriter/pseuds/LazySintastic13
Summary: As if Red wasn't going to try to bust himself out.





	Prison Break ... Not

**Author's Note:**

  * For [silverryu25](https://archiveofourown.org/users/silverryu25/gifts).



He’d plan everything with meticulous care: from the trading, to socializing, and even flirting with a couple of inmates and guards here and there. All to gather the necessary information and tools.

Stuck in this boring dump for a whole fucking month, a place where magic was nullified due to the cuff attached to their ankle, like hell he wouldn’t break out.

He actually has shit to do. Direct orders from the boss can’t be ignored. And this whole prison business had gotten him way behind schedule.

The short skeleton didn’t need to bother dwelling at the moment how he got caught—how he got seen and who reported him. He’ll think about it after he escaped.

A small growl managed to slip from his mouth at the reminder of how his mission had been going so well. If he actually managed to find out who was responsible, he’ll make sure to kill the stupid fuck for giving him more work.

* * *

Night came about quick, and it was time for Red to make his move.

He took out the small cloth bag hidden in his person. It was filled with countless of wires and a sheet of metal shaped into tweezers he’d managed to accumulate. Substitutes for a lock pick set.

Red, unfortunately, couldn’t unlock the cuff so easily, but he knows where the right key was located. He’ll just have to get it from there without being seen.

Getting out of the cell was the easiest of his tasks. The harder part is what followed after.

Avoiding the patrol guards.

He had a paper crammed full of the days of the week, time, and guard names in small letters—the night watch schedule he made from scratch.

There were a lot of long-time convicts on the first floor who’d grasped the night watch’s round schedules. So he had to personally ask them about the patterns for the week in exchange for getting them a lawyer to plead their case in court. Nothing ever came free in life after all. It was a good thing that despite not being too high ranked in the famiglia, what he got were strong connections. He’ll get them their lawyers, and whether they’ll succeed or not ain’t his problem.

Though Red had to admit, it was a downright pain in the ass in straightening out the contradictions after listening to several people’s accounts. There shouldn’t be any problem with the information he’d gathered, but there will be that tinge of apprehension he cannot rid of. 

After all, he can’t exactly know if some of the information he’d be given were lies, and this was his first, and most likely last as well, escape. There were no attempts. It was either he escaped, or he gets a heavier sentence and a tighter watch on him. He wouldn’t be able to leave if that happened.

Red gritted his teeth, and took a step forward out of his cell. He’ll just have to gamble.

* * *

So far so good. Hiding behind pillars, stealthily rushing out towards another column, hugging the walls, it looked like his information was indeed correct. Granted, he had a few close calls, but he managed to get around not being spotted.

Now, he stood to picklock the door he needed to get in with ease and headed inside.

_Good._

There were no guards, so Red immediately went towards the board where all the keys hung. 

However, just as he was about to take the key that was going to unlock his restraining cuff—

_Ping._

Red gasped when a blue soul held his body still and slammed him to the opposite wall.

The impact on his back made the skeleton dizzy as he groaned.

“Heh, I knew you were up to something.”

Red’s eye lights dilated in surprise, before it narrowed as he glared.

_“You.”_

Sans.

The one officer he always held guard up against.

Despite that mellow attitude, and had even downright shared jokes and flirted back, Red had a gut feeling that there had always been something more to him. 

He had been careful. In fact, Sans wasn’t even supposed to be here. He was sure of it.

Red thought that he had gotten the fucker off his tail when he played it cool for a whole week. To think that the monster was just bidding his time; observing and waiting for Red to make the move to strike there and then.

He’d been completely fooled.

Sans popped right in front him, eye socket flaring with magic whilst eye lights were coloured deep blues.

It sent a shudder down Red’s spine when he saw the intimidating look. He began to break out in cold sweat, and by carefully weighing out his choices, he should’ve of opted to stay quiet—to not provoke the one in power when he’s rightfully the one in the disadvantage.

But fuck if the monster in front of him doesn’t look hot. How could he not get turned on?

Red braced himself, summoning the courage to not look like he’d at least about to piss himself silly. He started with a chuckle before he gave Sans a coy smile with lidded eyes. “So, are you going to _discipline_ me?” He made sure to put emphasis on the word to make sure the other knew exactly what he was insinuating. “Show me a _bad_ time?” His eyes slowly trailed down Sans’ body to rest his sight on the crotch. He smirked when he saw the hint of blue glowing beneath the fabric. “With your _cock?”_ He uttered the last word with the lilt of questioning innocence; as if the word was foreign to him.

Sans was immediately on him, their mouths crashing painfully against each other, and their tongues instantly fought for dominance in the heated battle.

But with Sans having the upper hand, Red gasped when the guard’s wandering hands found their way to caress his pelvis beneath the clothes.

He found himself being overwhelmed, as if he was being devoured completely. Their saliva mixed and slid down their jaws. And Red had to push away to catch his breath.

They were both panting, staring at each other with hunger and lust.

Well, being so eager, Red surely did not want to disappoint. But he couldn’t do much since he couldn’t summon his magic.

So Red gave Sans a sultry smile. “Too bad I can’t summon up my magic. I’d have made a plump ass for you to fondle by now.”

Sans snorted, but didn’t say a word for a while. “... If you promised to give me your word that you won’t teleport after I release you, I’ll do it.”

Red sniggered. “You want to fuck me that much?”

The hands on him pulled forward so that he was pressed against Sans; chest to chest. Red was a bit irked that he had to gaze up because of the latter being slightly taller than him.

Sans voice drop an octave, and Red shivered when he heard it. “You want this too, you _slut.”_

The growl at the end had Red more than willing to just spread his legs. He inwardly cursed. It had to be illegal to be this downright sexy.

But he had to promise. And that was a big deal.

Red was not one to go back on his word.

On one hand, he gets freed and gets laid to boot. But on the other hand, that meant he’ll have a hard time escaping afterwards. He highly doubted Sans would let him go just because they had a one-off.

Weighing his options in his mind, Red met Sans’ gaze head on. “... I promise ... not to teleport after you free me.” There. He said it. Now fuck him.

Red better get the fuck he deserved. So he added with a growl. “You better fuck me good. Or else.”

His empty threat made Sans chuckle darkly. More amused than anything before the skeleton used his magic to summon up the key, and maneuvered it to unlock the cuff. He didn’t want to take his hands away after all.

Once Red was freed, the prisoner hummed in relief, feeling his magic return in his core. “That’s feels better.”

And moments later, Sans felt the uniform fill up, and his hands now squeezed the plumped ass he was promised.

Red grinned. “Are we gonna fuck, or what?”

Sans growled. He inwardly promised to himself that he was going to make this slut scream and completely _fucked_ when he was done with him.

But just as they were about to start, the knock on the door startled them both.  _Oh shit._

After a quick knock, Papyrus entered the room. Then questionably looked at Sans, who sat behind the work desk. “Sans? Why are you here?”

“Oh, you know, just thought to check on some files.” Sans smiled nonchalantly, waving a folder as proof.

“Oh, I see. I also need to find some files myself. Do you happen to know where I could get the file for inmate 0LS13?”

“Sure do. Should be in that box on the top left corner of the shelf.”

“Oh, thank you brother.”

“No problem, Paps.”

It was lucky that the desk was situated across from the door. And the shelf he spoke of was on the opposite wall where the board with the keys was right beside it.

“Goodness me. It’ll take forever to find that file in this mess.” Upon opening the box, Papyrus saw the clutter of papers. But it was a task he wasn’t going to back down to. And thus got to work.

Meanwhile, Sans got his plate full of troubles.

Because a certain little vixen decided to be playful.

Ever since Papyrus came, Red had gotten the wonderful idea of getting back at Sans; especially since the other’s hands laid on top of the desk.

Hiding under the table, in between Sans’ legs with the glowing bulge practically in front of his face, how could a slut like him resist?

Red slowly opened his mouth, his hot tongue lewdly hung out as he leaned forward to lick at the bulge. He lathered up the outline of the cock, wetting the fabric thoroughly as he gave a few quick sucks when the shape became more pronounced beneath the clothe.

Red smirked when he felt the other freeze up, but that wasn’t going to stop him. Getting a bit bolder, he used his teeth to grab the zipper, and slowly pulled it back. 

He felt a little disappointed that the other wore underwear or else he would’ve already gotten his prize. Well, it would have to do.

Red nuzzled the length through the garment. The musky smell filled his senses, sending waves of heat through his core. Without another moment, he encased his mouth over the outline of the head and sucked; making sure to continue lathering it with his tongue.

Sans bore the treatment with gritted teeth. He was beginning to sweat as he repressed himself from gasping and groaning.

He wanted to so badly pull out his cock and fuck the other’s mouth. But with his brother in the room ... _Fuck it._

Red was startled when a hand grabbed his skull to move it away from his meal. He was about to mutter a complaint when his eyes widened in surprise. Sans pulled his pants down enough for his blue cock to spring out and it was much larger than Red expected.

Red’s mouth began to water, and he actually gulped before nearing the monster. The hand, he remembered vaguely, helped guide him along to the pulsing length. And almost immediately, Red opened his mouth for his tongue to curiously lick the tip.

Sans suppressed the urge to just fuck Red’s mouth then and there. It’ll make too much noise, and he definitely didn’t want Papyrus to get suspicious. Sans breathed heavily, he’ll have to go along with Red’s pace until Papyrus left.

Unable to hold back, Red opened wide and immediately swallowed past the bulbous head; taking it halfway deep down his makeshift throat. 

 _Fuuck._ Sans was losing his mind. The feeling of that sinful mouth bob on his cock, the heat and stimulation it came with was almost enough to shatter his restraint. Hazily, he looked at Papyrus who still had his back faced to him.

… Sans licked his mouth. _Oh it’s on._

Red’s jaw was beginning to ache from the sheer girth, and he was frustratingly unable to take it all in without choking. Suddenly, he was pulled by the hand on his head at the same time Sans had pushed his chair in and slammed the cock in him.

Tears formed from the assault, having to adjust his throat to take it all in. Red would glare at Sans if he had half the mind to bother concentrating on it. Instead, the skeleton himself didn’t realize that his eye lights formed trembling hearts as his body twitched and shook from the rough treatment. It didn’t help that he wanted to whimper when his head was being gently caressed; as if praising him from doing a well done job in taking the whole length in him.

The guard’s bones lightly rattled in pleasure. He could feel that soft throat milking his firm cock every time Red swallowed. And when Sans had the chance to look down, he couldn’t help but feel enlightened at the sight of Red’s teary face. He knew that if he could, he would see the glowing blue bulging through the other’s throat. And that image alone made him want to cum then and there.

It really was a good thing that skeleton monsters like them didn’t need to truly breathe. And Sans gained himself a cock warmer in return.

Red didn’t know how long he was stuck like that, swallowing and being pushed deeper so that his nose was flushed against the fabric of the other’s pants. He desperately wanted to rub himself off. And he was sure that his holes were already dripping wet, twitching to be filled—to be thoroughly fucked. But now, he was nothing more than a mouth pussy to warm up and hold cock, drooling all over it as he continued to undulate his throat. He felt proud that he managed to hear short quick gasps from the guard. And when he managed to look up, his whole body shuddered with delight in seeing the raw desire in those deep blue eye lights.

Red vaguely heard the sound of the door before Sans spoke lowly. “Hold on tight.”

Both hands suddenly grabbed onto his head and Sans began to fuck his throat in earnest; rolling his hips against Red’s face as he slammed in with every thrust, not bothering to give the skeleton any reprieve.

Red could only moan from the assault, his hands were forced to grip tight onto the other’s pants from and more tears cropped up in his sockets.

“Heh, ya really like getting your mouth fucked? Who knew you were such a cock sucker.”

Sans cussed when Red moaned loudly in response, having long forgotten to bother staying quiet. The vibrations done on his cock made him completely lose it, and Sans groaned harshly.

Red could feel the head squirt a bit, coating his throat, making him suck even harder on impulse.

At that, Sans pulled Red back and he watched the copious amount of drool drench his cock and thickly connect with other’s tongue that fell out and panted with need. He chuckled at the broken whine. “Don’t worry. I’ll give it to you.”

The next thing Red knew, he was against the wall and his pants was gone. His breath hitched when he felt arms go under his knees to lift him up and spread him open; unable to hide his dripping wet cunt and the fluttering hole beneath it, both aching to be filled.

He looked up to see Sans smirking, lining up the tip to his puffy folds. “I’d like to see you try leaving after I'm done with you.”

“… H-hehe.” Red smiled crookedly, but the challenge was evident in his eyes. “I-If it means g-getting fucked silly. I-I don’t see why I w-wouldn’t try again.”

“You make a fair point.”

And Red keened when that monstrous cock hilted in his pussy in one-go. His juices gushed, making a mess on the floor, and his body rattled with his tongue lolled out.

“Oh? You came already? How cute.”

Red’s screams were swallowed by Sans, their tongues meshing messily as the latter continued the rough assault. He didn’t get to hear what Sans said as he lost himself to the overwhelming pleasurable sensations.

“Heh, looks like I better thank Fell for the gift. From a Don to another Don indeed.” Sans didn’t think that Fell would actually give him his brother to settle an alliance with his own famiglia. Even going as far to set up the whole thing; from the mission, to getting caught, and to even having Sans’ own men play along as inmates that helped give Red everything he needed to ‘escape’.

And for the life him, Sans can’t say he hated it as he came inside the tight convulsing heat, coating it thoroughly with his essence and causing Red to become an even more babbled mess; coming for the umpteenth time. He slowly removed his still hardened length from the cum-filled cunt, and then pushed through the fluttering hole beneath. 

Sans didn’t hate it at all.

**Author's Note:**

> Yes. Yes I did that. :D  
> I tried anyway. XD
> 
> Hope you like your gift Ryu~!


End file.
